2 Groomsmen Proposal Gifts for the Guys You Love (2023)

groomsmen proposal gifts

If there’s one way to make your wedding the most memorable event of your life, it’s by incorporating your buddies. Here are 25+ creative and funny groomsmen proposal gifts that perfectly describe the relationship you have with the boys.

You might be wondering how to ask someone to be your groomsmen. With these groomsmen gift ideas, you’ll pop the question in a unique fashion. Start your marriage off properly, and that’s with your buddies right by your side!

Groomsmen Proposal Whiskey Label

1. Groomsmen Proposal Whiskey Label

Here’s one excellent method to dress up a regular old bottle of whiskey. Slap it on, and you’ll have one of the best groomsmen proposal ideas ever. It’s time to drink up and party; a wedding is on its way! There you have it – classy and unique.


2. Personalized Engraved Football

If your guy is the MVP in your life, he deserves to know it. Tell him how valuable he is. If you need best man proposal ideas, try throwing him this football. He won’t know what hit him. This will be the one time he won’t fumble.

 Custom Can Cooler

3. Custom Can Cooler

When you say, “Be my groomsman,” with this pretty can cooler, your guy will never say no. In fact, he’ll be so honored you’re asking him. And when he agrees, you know what’s going to happen. You guys will have a drink and put the gift to good use.

Groomsman Proposal Shoebox

4. Groomsman Proposal Shoebox

It’s time to bring proposals to a whole new level with this groomsmen gift box. Get each of your fellas to say yes with items packaged in style. As for the fillings, let your imagination go wild! Nothing is off-limits when it comes to these guys.

Will You Be Mine Groomsman Watch

5. Will You Be Mine Groomsman Watch

You won’t find a fancier groomsman proposal gift than this beautiful watch. In addition to being superbly personalized, it also comes in a pretty box with a lovely message. What a perfect way to put a smile on someone’s face! It’s definitely time to suit up.

Best Man Today Best Friend for Life Custom Photo Mug

6. Best Man Today Best Friend for Life Custom Photo Mug

When you’ve got a friend you can depend on for the rest of your life, be thankful. Show him how much you appreciate him with one of the nicest best man gifts available. He’ll love waking up to coffee served in a mug that means the world to him.

Engraved Throwing Axe

7. Engraved Throwing Axe

Are you ready for one of the best ideas for a groomsmen proposal? Gather your buddies and hand them the most iconic gifts they can imagine. This personalized axe guarantees a thrill and satisfying thud every time it hits the target. It’s time to go Celtic!

Engraved Lighter for Groomsmen - groomsmen proposal gifts

8. Engraved Lighter for Groomsmen

Are you racking your brain thinking about how to ask someone to be your groomsmen? Let this lighter do it for you. Complete with personalized engraving, this fire-starter is something that will stay in your guy’s pocket for many years to come. Is it time for cigars yet?

Personalized Wooden Cufflinks - groomsmen proposal gifts

9. Personalized Wooden Cufflinks

The best groomsmen invite ideas always involve a pair of classy cufflinks. Make this personalized gift a part of your bachelor party, and it’ll feel like you’re in Las Vegas. On that note, how about a weekend at the casino? That’s going to make things epic!

Groomsmen Personalized Baseball - groomsmen proposal gifts

10. Groomsmen Personalized Baseball

If you’re looking for creative groomsmen proposal gifts, here’s one every guy will jump on. This baseball fan will finally be speechless for once in his life, believe it or not. No gift will ever top yours. Once he says yes, it’s time to hit the field!

Cigar Gift Box

11. Cigar Gift Box

It goes without saying, but your best man and groomsmen are the people you can depend on, come what may. Show these guys how precious they are with cigar gift boxes that will impress. Now, all you have left to do is set up your man cave.

Personalized Groomsmen Socks - groomsmen proposal gifts

12. Personalized Groomsmen Socks

If there’s one thing every groom should say at his wedding, it’s, “Suit up, groomsmen!” With these socks around, your entourage will be the center of attention. Make sure to have the photographer around when everyone’s getting dressed. These gifts are the perfect photo op!

Funny Groomsmen Invitation - groomsmen proposal gifts

13. Funny Groomsmen Invitation

If you and your buddies find cursing therapeutic, these invites are a must-have. Hand-deliver them together with a funny groomsmen gift, and they won’t dare say no! Why would they, when your wedding is set to be the event of the season? They’ll even frame up their cards!

Groomsmen Flasks - groomsmen proposal gifts

14. Groomsmen Flasks

When you pop the important question, “Will you be my best man?” have this gift ready. Because the answer’s going to be a resounding yes, a drink will be in order. Pour it out with style from this beautiful personalized flask. It’s time to celebrate!

Leather Dopp Kit Bag - groomsmen proposal gifts

15. Leather Dopp Kit Bag

Girls aren’t the only ones with fancy toiletry bags. Here’s a leather-made beauty that’s perfect for your guys. When it comes to ways to ask guys to be groomsmen, this is it. And if you propose over a boys’ weekend, you’ll have a real reason to let loose!

Groomsmen Leather Personalized Poker Set - groomsmen proposal gifts

16. Groomsmen Leather Personalized Poker Set

Where’s the fun in boys’ night without some good old poker? If cool groomsmen proposal gift ideas are what you’re after, you’re going to jump at this. Personalized and practical, this set comes with cards, dice, and chips. All you need now are some cigars and whiskey.

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17. Will You Be My Groomsmen Puzzle Invitation

Forget offering traditional cards; you want the best groomsmen invitation ideas. Here’s one the guys are sure to love. This puzzle is fun, creative, and will surely elicit some smiles. Make sure you capture the expressions on video as they figure out the message! Truly priceless!

Groomsmen Pocket Watch - groomsmen proposal gifts

18. Groomsmen Pocket Watch

Have you ever seen such an elegant groomsmen proposal gifts? This pocket watch is nostalgic and comes engraved with a design of your choice. Your buddy is going to be telling everyone the time once it’s in his hands. Who can blame him, truly?

Custom Fishing Lure - groomsmen proposal gifts

19. Custom Fishing Lure

It’s the season for you and the guys to catch some bass and trout once again. This time, they’re getting some customized lures that pack a whole load of meaning. With these gorgeous fishing groomsmen proposal gifts as hooks, you can be sure to go home with a big catch!

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20. Groomsman Safety Razor

Personal grooming isn’t a question of pride; it’s simply about taking good care of oneself. This gift set stands tall among the great groomsman proposal gift ideas. Why? Well, you’re helping your friend look fantastic, and isn’t that what being a good companion is about?

WoodenWhiskey Barrel - groomsmen proposal gifts

21. Wooden Whiskey Barrel

In this gift, you’ll find a chance to bond, sip on the best drink ever, and enjoy life. Offer your best man and groomsmen authentic-looking barrels with fantastic surprises inside. They’re great as keepsakes, but will also come in handy for the upcoming boys’ nights.

Camping Mug - groomsmen proposal gifts

22. Camping Mug

Allow your guys to enjoy the great outdoors with an enamel mug that’s perfect for camping trips. If you’re hunting for a groomsman proposal gift, you’re staring at it! Nothing’s more welcoming than a hot cup of joe as one enjoys the sunrise. Get packing already!

Personalized Golf Balls

23. Personalized Golf Balls

Do you and your group love to hit the green every now and then? If so, these groomsmen golf gifts are just perfect for your proposal. Find a nice clear day and set it up. You can be sure they won’t be losing any of these balls!

Engraved Pocket Knives - groomsmen proposal gifts

24. Engraved Pocket Knives

Here’s something useful you can fit into your DIY groomsmen proposal box. These pretty pocket knives are the one utility tool every man should hold in their camping gear. If your guy friends love the outdoors, they’re going to go nuts for this durable gift!

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25. Funny Best Man Card

The best man proposal of a lifetime involves beers, games, and hilarity. Here’s one vital ingredient to inject some humor into your question. This card makes fun of the way men just don’t talk about mushy stuff. If this is how you communicate, get it now!

groomsmen proposal gifts

26. Groomsmen Proposal Star Wars Digital File

If you’re ready to ask your friend, “Will you be my groomsman?” do it the Star Wars way. Print out these unbelievably cool cards to invite the whole gang to join your force. Once that’s done, it’s only apt that you re-watch the whole saga together!

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